Triisopropyl borate → 2-Methoxy-5-(trifluoromethyl)phenylboronic acid

Temperature

-78 °C

n-Butyl lithium (1.6M in hexanes, 456 μL, 0.729 mmol) was added dropwise to a stirred solution of 2-iodo-1-methoxy-4-(trifluoromethyl)benzene (Step A, 200 mg, 0.662 mmol) in THF (1.5 mL) at −78° C. under an atmosphere of nitrogen. The reaction stirred at −78° C. for 30 min prior to the addition of triisopropyl borate (458 μL, 1.986 mmol). The reaction stirred an additional 2 h at −78° C. and was quenched with sat. NH4Cl. The mixture was extracted with CH2Cl2 and the organic phase was washed with NaHCO3 (15 mL) and brine (15 mL), dried (Na2SO4), filtered, conc. in vacuo to afford [2-methoxy-5-(trifluoromethyl)phenyl] boronic acid which was carried on without purification.

1. stirringThe reaction stirred an additional 2 h at −78° C.
2. customwas quenched with sat. NH4Cl
3. extractionThe mixture was extracted with CH2Cl2
4. washthe organic phase was washed with NaHCO3 (15 mL) and brine (15 mL)
5. dry with materialdried (Na2SO4)
6. filtrationfiltered, conc. in vacuo

ORD record

ord-0412635863374b26869bb505e5c3d4c0

Source dataset

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07652049B2